Hydrochloric Acid → HCID 67271478, compound

HRID 250252Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11](Br)=[C:12](OC)[CH:13]=2)[N:8]([CH:18]2[CH2:20][CH2:19]2)[C:7]=1[CH3:21])=[O:5])[CH3:2].[CH3:22][C:23]1[CH:24]=[C:25]([OH:38])[CH:26]=[CH:27][C:28]=1B1OC(C)(C)C(C)(C)O1.[C:39](=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C.CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:28]3[CH:27]=[CH:26][C:25]([OH:38])=[CH:24][C:23]=3[CH3:22])=[C:12]([CH3:39])[CH:13]=2)[N:8]([CH:18]2[CH2:20][CH2:19]2)[C:7]=1[CH3:21])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 6-bromo-1-cyclopropyl-5-methoxy-2-methyl-1H-indole-3-carboxylic acid ethyl ester (355 mg, 1.01 mmol), 3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (472 mg, 2.20 mmol), tetrakis(triphenylphosphene)palladium (87 mg, 0.075 mmol), aqueous sodium carbonate (2 M, 3.0 mL, 6.00 mmol), DMF (5.9 mL) and ethanol (5.9 mL) is heated under nitrogen at 85° C. for 4 h. The mixture is acidified with 1 N HCl and extracted with ethyl acetate. The ethyl acetate layers are combined and washed with water and brine and dried over MgSO4. The residue is purified via flash chromatography eluting with THF-heptane (25→40%) to afford the title compound (187 mg, 49%) as a white solid. ES/MS m/e 380.0 (M+1).

Workup

extractionextracted with ethyl acetate
washwashed with water and brine
dry with materialdried over MgSO4
customThe residue is purified via flash chromatography
washeluting with THF-heptane (25→40%)

Sources & evidence

ORD record: ord-971fda9ed65a45f58c5c8a265030f757
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863302B2

Reaction notes

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