4-Isopropylphenylboronic acid → Methyl 4-[(4-methylethylphenyl)amino]-5-methylthiothiophene-2-carboxylate

HRID 1058482Notes

Reaction equation

HRID 1058482 reaction equation
C[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:12]=[C:13]([C:17]([O:19][CH3:20])=[S:18])[S:14][C:15]=2[CH3:16])=[CH:6][CH:5]=1)C.N[C:22]1C=C(C(OC)=S)S[C:26]=1C.C(C1C=CC(B(O)O)=CC=1)(C)C>>[CH3:2][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]2[CH:12]=[C:13]([C:17]([O:19][CH3:20])=[S:18])[S:14][C:15]=2[CH3:16])=[C:8]([CH2:22][CH3:26])[CH:9]=1

Participants

4

Reactant 3

HCID 27734804-Isopropylphenylboronic acidHCID 86583855Methyl 4-{[4-(methylethyl)phenyl]amino}-5-methylthiothiophene-2-carboxylateHCID 86583856Methyl 4-amino-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583854Methyl 4-[(4-methylethylphenyl)amino]-5-methylthiothiophene-2-carboxylateYield 12.5%

Procedure

Methyl 4-{[4-(methylethyl)phenyl]amino}-5-methylthiothiophene-2-carboxylate: Using a procedure similar to Example 208, step (a), 74.4 mg (0.36 mmol) of methyl 4-amino-5-methylthiothiophene-2-carboxylate was allowed to react with 118 mg (2 equiv, 0.72 mmol) of 4-isopropylphenyl boronic acid to give 14.5 mg (12.5%) of methyl 4-[(4-methylethylphenyl)amino]-5-methylthiothiophene-2-carboxylate. 1H NMR (CDCl3, 400 MHz) δ 1.26 (d, 6H, J=6.2 Hz), 2.39 (s, 3H), 2.89 (m, 1H), 3.89 (s, 3H), 6.98-7.01 (m, 2H), 7.17-7.19 (m, 2H), 7.73 (s, 1H).

Sources & evidence

ORD record
ord-21579b9ea1ed4bc2bdc3f92522278b07
Source dataset
uspto-grants-2003_02
Patent number
US06515002B2

Reaction notes

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