Sodium Bicarbonate → HCID 178502329, compound

HRID 1751607Notes

Reaction equation

HRID 1751607 reaction equation
[CH3:1][CH:2]([CH3:38])[C@H:3]([NH:33][C:34](=[O:37])[O:35][CH3:36])[C:4](=[O:32])[N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:14][C:13]2[C:15]3[C:20]([CH:21]=[CH:22][C:12]=2[N:11]=1)=[CH:19][C:18](B1OC(C)(C)C(C)(C)O1)=[CH:17][CH:16]=3.Br[C:40]1[CH:41]=[C:42]2[C:47](=[CH:48][CH:49]=1)[C:46]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[C:45]([NH:58][C:59](=[O:61])[O-:60])[CH:44]=[CH:43]2.C([O-])(O)=O.[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH3:36][O:35][C:34](=[O:37])[NH:33][C@@H:3]([CH:2]([CH3:1])[CH3:38])[C:4]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:11][C:12]2[C:22]3[C:17]([CH:16]=[CH:15][C:13]=2[N:14]=1)=[CH:18][C:19]([C:40]1[CH:49]=[CH:48][C:47]2[C:42](=[CH:43][CH:44]=[C:45]([NH:58][C:59]([O:60][C:2]([CH3:38])([CH3:3])[CH3:1])=[O:61])[C:46]=2[NH:50][C:51]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:57])[CH:41]=1)=[CH:20][CH:21]=3)=[O:32]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 131733638Tert-butyl 6-bromonaphthalene-1,2-diyldicarbamateHCID 178502307HCID 178502307, compound

Product 1

HCID 178502329HCID 178502329, compoundYield 151.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To methyl (S)-3-methyl-1-oxo-1-((S)-2-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate (190 mg, 0.36 mmol), tert-butyl 6-bromonaphthalene-1,2-diyldicarbamate (205 mg, 0.47 mmol), Pd(PPh3)4 (42 mg, 0.036 mmol). DME (1.5 mL) was added and followed by 1.08 mL 1M NaHCO3 aqueous solution. The reaction was purged with Ar and heated to 120° C. at microwave synthesizer for 0.5 hour. The reaction was cooled to room temperature and concentrated down. EtOAc was added and washed with sat. NaHCO3 aqueous (2×) and sat. NaCl aqueous (1×). The organic layer was concentrated down after drying over sodium sulfate and subject to silica gel chromatography with an eluent of ethyl acetate and hexane at a gradient of 40-100% with an ISCO column (12 g silica gel). The fractions containing product were combined and the solvent was removed under reduced pressure to provide the desired product (205 mg, 75%). MS (ESI) m/z 752 [M+H]+.

Workup

  1. customThe reaction was purged with Ar
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated down
  4. additionEtOAc was added
  5. washwashed with sat. NaHCO3 aqueous (2×) and sat. NaCl aqueous (1×)
  6. concentrationThe organic layer was concentrated down
  7. dry with materialafter drying over sodium sulfate
  8. additionThe fractions containing product
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5ec1e88170954449850b56e700061970
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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