Sodium Carbonate → 2-[1-(cyclopropylmethyl)-5-(2-thienyl)-1H-indol-3-yl]acetic acid

HRID 2301662Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH:12]1[CH2:14][CH2:13]1)[CH:6]=[C:5]2[CH2:15][C:16]([OH:18])=[O:17].[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1.CCO.O>[CH:12]1([CH2:11][N:7]2[C:8]3[C:4](=[CH:3][C:2]([C:20]4[S:19][CH:23]=[CH:22][CH:21]=4)=[CH:10][CH:9]=3)[C:5]([CH2:15][C:16]([OH:18])=[O:17])=[CH:6]2)[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a sealed tube containing 2-[5-bromo-1-(cyclopropylmethyl)-1H-indol-3-yl]acetic acid (100 mg, 0.32 mmol), 2-thiopheneboronic acid (124 mg, 0.97 mmol), (C6H5)4Pd (37 mg, 0.032 mmol), Na2CO3 (2.6 mmol) in a mixture of benzene/EtOH/H2O (5/1/3, 4.5 mL) was heated at 85° C. for 19 h. The mixture was poured onto diethyl ether and adjusted to pH 3 before extracting with diethyl ether. The mixture was washed with NaH2PO4, dried over MgSO4 and evaporated to give the crude product which was purified on silica gel column (33% EtOAc in hexane with 1% HCOOH) to give 79 mg (78% yield) of the product.

Workup

additionThe mixture was poured onto diethyl ether
extractionbefore extracting with diethyl ether
washThe mixture was washed with NaH2PO4
dry with materialdried over MgSO4
customevaporated
customto give the crude product which
customwas purified on silica gel column (33% EtOAc in hexane with 1% HCOOH)

Sources & evidence

ORD record: ord-79fec7a210994b3ab945aa73c12007bd
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500853B1

Reaction notes

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