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Potassium Carbonate → 5-{5-[(cyclopropylamino)methyl]-2-thienyl}-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

HRID 562139
Notes
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Reaction equation

HRID 562139 reaction equation
[CH:1]1([NH:4][CH2:5][C:6]2[S:10][C:9](B(O)O)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.Br[C:15]1[CH:16]=[C:17]2[C:21](=[C:22]([C:24]([NH2:26])=[O:25])[CH:23]=1)[NH:20][CH:19]=[C:18]2[CH:27]1[CH2:32][CH2:31][N:30]([S:33]([CH2:36][CH3:37])(=[O:35])=[O:34])[CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]1([NH:4][CH2:5][C:6]2[S:10][C:9]([C:15]3[CH:16]=[C:17]4[C:21](=[C:22]([C:24]([NH2:26])=[O:25])[CH:23]=3)[NH:20][CH:19]=[C:18]4[CH:27]3[CH2:28][CH2:29][N:30]([S:33]([CH2:36][CH3:37])(=[O:34])=[O:35])[CH2:31][CH2:32]3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113844275-bromo-3-[1-(ethanesulfonyl)-4-piperidinyl]-1H-indole-7-carboxamideHCID 66722847{5-[(Cyclopropylamino)methyl]-2-thienyl}boronic acid

Product 1

HCID 577328365-{5-[(cyclopropylamino)methyl]-2-thienyl}-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

Reagents, catalysts & solvents 1

HCID 178418397
HCID 178418397, compound
Catalyst

Procedure

Following the general procedure of 5-{5-[(ethylamino)methyl]-2-thienyl}-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide, (5-formyl-2-thienyl)boronic acid (50 mg, 0.32 mmol), cyclopropylamine (0.022 mL, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 63 mg of crude {5-[(cyclopropylamino)methyl]-2-thienyl}boronic acid. The crude {5-[(cyclopropylamino)methyl]-2-thienyl}boronic acid was then reacted with 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (80 mg, 0.193 mmol), potassium carbonate (160 mg, 1.16 mmol), and tetrakis(triphenylphosphine)palladium(0) (5 mg, 0.004 mmol) to give impure title compound. The impure title compound was purified again with the Agilent MDAP and isolated as the free base according to the procedure shown in Example 5 to give 6.8 mg of the title compound (7.2%).

Sources & evidence

ORD record
ord-7aa286559fdf46ba88e6dda7809715f6
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063071B2

Reaction notes

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