Sodium Carbonate → HCID 59568617, compound

HRID 216936Notes

Reaction equation

[NH2:1][C:2](=[O:29])[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[F:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:36]=1[F:37].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[NH2:1][C:2](=[O:29])[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:34]2[CH:33]=[CH:32][C:31]([F:30])=[C:36]([F:37])[CH:35]=2)=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 85 °C

Procedure

(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iii), 300 mg) and 3,4-difluorophenylboronic acid (92 mg) in acetonitrile (8 mL) were treated with aqueous sodium carbonate solution (2M, 0.58 mL) and nitrogen was bubbled through the reaction mixture. 1,1 bis(Di-tert-butylphosphino)ferrocene palladium dichloride (8 mg) was added and the mixture was heated at 85° C. for 18 h. The mixture was purified by chromatography on silica eluting with 50-100% ethyl acetate/isohexane as eluent to yield the sub-titled compound (305 mg).

Workup

customwas bubbled through the reaction mixture
addition1,1 bis(Di-tert-butylphosphino)ferrocene palladium dichloride (8 mg) was added
customThe mixture was purified by chromatography on silica eluting with 50-100% ethyl acetate/isohexane as eluent

Sources & evidence

ORD record: ord-ec90f6832db246d6b644e4b11638cd65
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193239B2

Reaction notes

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