Acetonitrile → HCID 67437567, compound

HRID 1968865Notes

Reaction equation

HRID 1968865 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C@H:8]([CH2:13][N:14]([C:27]1[CH:32]=[CH:31][C:30](Br)=[CH:29][CH:28]=1)[C:15]([C@@H:17]1[CH2:19][C@H:18]1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=1)=[O:16])[C@@H:9]([CH3:12])[CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].B(O)O.[C:38]([O-:41])([O-])=O.[K+].[K+].[CH3:44][C:45]#N>CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:1]([O:5][C:6](=[O:34])[NH:7][C@H:8]([CH2:13][N:14]([C:15]([C@@H:17]1[CH2:19][C@H:18]1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=1)=[O:16])[C:27]1[CH:32]=[CH:31][C:30]([C:9]2[CH:10]=[CH:11][C:45]([CH2:44][O:41][CH3:38])=[CH:13][CH:8]=2)=[CH:29][CH:28]=1)[C@@H:9]([CH3:12])[CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 61668Boronic AcidHCID 67437961HCID 67437961, compound

Product 1

HCID 67437567HCID 67437567, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 80 mg (0.15 mmol) of the aryl bromide, [(1S,2S)-1-({(4-bromo-phenyl)-[(trans)-2-(5-fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-amino}-methyl)-2-methyl-butyl]-carbamic acid tert-butyl ester, in a microwave vial was added boronic acid (26 mg, 0.158 mmol), K2CO3 (41.5 mg, 0.301 mmol), PdCl2(PPh3)2 (5.3 mg, 0.008 mmol), 6 mL of MeCN, and 1 mL of water. The resulting mixture was microwaved at 140° C. for 30 min. It was then diluted with EtOAc, washed with water, brine and concentrated, and then purified in the neutral PREP HPLC to give 62 mg (72%) of the desired product.

Workup

  1. customThe resulting mixture was microwaved at 140° C. for 30 min
  2. washwashed with water, brine
  3. concentrationconcentrated
  4. custompurified in the neutral PREP HPLC

Sources & evidence

ORD record
ord-11763ee17f524ad4b470583f88a95ec4
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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