Potassium Carbonate → HCID 178502309, compound

HRID 1751351Notes

Reaction equation

HRID 1751351 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:39][C:40]1[CH:41]=[CH:42][C:43]2[CH:47]=[C:46](I)[S:45][C:44]=2[CH:49]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.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>[Br:39][C:40]1[CH:41]=[CH:42][C:43]2[CH:47]=[C:46]([C:18]3[CH:19]=[C:20]4[C:15](=[CH:16][CH:17]=3)[C:13]3[NH:14][C:10]([C@@H:6]5[CH2:7][CH2:8][CH2:9][N:5]5[C:4](=[O:32])[C@@H:3]([NH:33][C:34](=[O:37])[O:35][CH3:36])[CH:2]([CH3:38])[CH3:1])=[N:11][C:12]=3[CH:22]=[CH:21]4)[S:45][C:44]=2[CH:49]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 696728346-Bromo-2-iodobenzo[b]thiopheneHCID 178502307HCID 178502307, compound

Product 1

HCID 178502309HCID 178502309, compoundYield 152.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 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 (251 mg, 0.48 mmol) in DME (5 mL) was added 6-bromo-2-iodobenzo[b]thiophene (82 mg, 0.24 mmol), Pd(PPh3)4 (28 mg, 0.024 mmol), and K2CO3 (2M in H2O, 0.8 mL, 1.58 mmol). The solution was degassed with N2 for 10 min, then heated to 85° C. for 24 h. The mixture was cooled to rt, diluted with EtOAc, and washed with sat. NaHCO3, brine, dried with MgSO4, and concentrated. The residue was purified by silica gel chromatography to yield product (221 mg).

Workup

  1. customThe solution was degassed with N2 for 10 min
  2. temperatureThe mixture was cooled to rt
  3. additiondiluted with EtOAc
  4. washwashed with sat. NaHCO3, brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-03b494c4bc294ff0bb6b3d2435dee1ac
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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