3-Isopropylbenzeneboronic acid → Methyl 4-[(3-methylethylphenyl)amino]-5-methylthiothiophene-2-carboxylate

HRID 412980Notes

Reaction equation

HRID 412980 reaction equation
C[CH:2]([C:4]1[CH:5]=[C:6]([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:7]=[CH:8][CH:9]=1)C.N[C:22]1C=C(C(OC)=S)S[C:26]=1C.C(C1C=C(B(O)O)C=CC=1)(C)C>>[CH3:2][C:4]1[C:5]([CH2:22][CH3:26])=[C:6]([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:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 27734783-Isopropylbenzeneboronic acidHCID 86583853Methyl 4-{[3-(methylethyl)phenyl]amino}-5-methylthiothiophene-2-carboxylateHCID 86583856Methyl 4-amino-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86584792Methyl 4-[(3-methylethylphenyl)amino]-5-methylthiothiophene-2-carboxylateYield 19.5%

Procedure

Methyl 4-{[3-(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 3-isopropylphenyl boronic acid to give 22.6 mg (19.5%) of methyl 4-[(3-methylethylphenyl)amino]-5-methylthiothiophene-2-carboxylate. 1H NMR (CDCl3, 400 MHz) δ 1.27 (d, 6H, J=6.9 Hz), 2.40 (s, 3H), 2.89 (m, 1H), 3.88 (s, 3H), 6.15 (s, 1H), 6.86-6.89 (m, 3H), 7.24 (m, 1H), 7.77 (s, 1H).

Sources & evidence

ORD record
ord-6057662657ad4a448e1e8166cbba9f11
Source dataset
uspto-grants-2003_05
Patent number
US06562840B1

Reaction notes

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