Potassium Phosphate, Tribasic → HCID 71074710, compound

HRID 1852037Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]4[C:30]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:25][CH:24]=2)[C:17]([CH3:42])=[C:16]3[CH3:43])=[O:12])[CH3:9])=[N:6][CH:7]=1.[CH:44]1(B(O)O)[CH2:46][CH2:45]1.P(C1CCCCC1)(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:44]1([C:2]2[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]5[C:30]([C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])=[CH:31][CH:32]=[CH:33][CH:34]=5)=[CH:25][CH:24]=3)[C:17]([CH3:42])=[C:16]4[CH3:43])=[O:12])[CH3:9])=[N:6][CH:7]=2)[CH2:46][CH2:45]1

Participants

Conditions

Temperature: 100 °C

Procedure

A high-pressure vial was filled with the (S)-tert-butyl 4′-((5-((1-(5-bromopyridin-2-yl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylate (50 mg, 0.078 mmol), cyclopropylboronic acid (8 mg, 0.09 mmol, 1.2 equiv), Pd(OAc)2 (12 mg, 0.055 mmol, 0.7 equiv), (Cy)3P (8.7 mg, 0.031 mmol, 0.4 equiv), K3PO4 (49 mg, 0.23 mmol, 3 equiv), in toluene-water (10%). The reaction mixture was heated at 100° C. for 3 h under microwaves. The mixture was evaporated in vacuo to obtain the crude which was purified by prep. HPLC (MeOH/Acetonitrile/water) to obtain the title compound.

Workup

customThe mixture was evaporated in vacuo
customto obtain the crude which
customwas purified by prep

Sources & evidence

ORD record: ord-37925f49fe8e4412a32d51686abef2be
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957093B2

Reaction notes

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