Dichloromethane → 5-[5-(Cyclopropylmethyl)-3-thienyl]-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole

HRID 387347Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:7][CH:8]2[CH2:10][CH2:9]2)[S:5][CH:6]=1.[O:11]=[S:12]1(=[O:39])[CH2:17][CH2:16][CH:15]([C:18]2[C:26]3[C:21](=[C:22](C(N)=O)[CH:23]=[C:24](B4OC(C)(C)C(C)(C)O4)[CH:25]=3)[NH:20][CH:19]=2)[CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O1CCOCC1.O>[CH:8]1([CH2:7][C:4]2[S:5][CH:6]=[C:2]([C:24]3[CH:25]=[C:26]4[C:21](=[CH:22][CH:23]=3)[NH:20][CH:19]=[C:18]4[CH:15]3[CH2:16][CH2:17][S:12](=[O:11])(=[O:39])[CH2:13][CH2:14]3)[CH:3]=2)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

4-Bromo-2-(cyclopropylmethyl)thiophene (50 mg, 0.23 mmol), 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (80 mg, 0.19 mmol) and K2CO3 (105 mg, 0.76 mmol) was taken up in 1,4-dioxane (3 mL) and water (1.5 mL) in a microwave vial. The mixture was degassed by bubbling argon through it for 5 min. PdCl2(dppf).DCM adduct (25 mg, 0.031 mmol) was added, and the reaction was heated in a microwave for 5 min at 100° C. The reaction mixture was concentrated, diluted in DMSO, and purified on a Gilson HPLC(NH4OH buffer). The desired fractions were concentrated, giving 18 mg (22%) of the title compound.

Workup

customThe mixture was degassed
customby bubbling argon through it for 5 min
concentrationThe reaction mixture was concentrated
additiondiluted in DMSO
custompurified on a Gilson HPLC(NH4OH buffer)
concentrationThe desired fractions were concentrated

Sources & evidence

ORD record: ord-87c06667bb984ec6ac6c29b3baba11d2
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372875B2

Reaction notes

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