4-Butylphenylboronic acid → Methyl 4-[(4-butylphenyl)amino]-5-methylthiothiophene-2-carboxylate

HRID 2298676Notes

Reaction equation

HRID 2298676 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[S:9])[S:5][C:6]=1[CH3:7].[CH2:12]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)[CH2:13][CH2:14][CH3:15]>>[CH2:12]([C:16]1[CH:21]=[CH:20][C:19]([NH:1][C:2]2[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[S:9])[S:5][C:6]=2[CH3:7])=[CH:18][CH:17]=1)[CH2:13][CH2:14][CH3:15]

Participants

3

Reactant 2

HCID 41008604-Butylphenylboronic acidHCID 86583856Methyl 4-amino-5-methylthiothiophene-2-carboxylate

Product 1

HCID 86583858Methyl 4-[(4-butylphenyl)amino]-5-methylthiothiophene-2-carboxylateYield 19.3%

Procedure

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 128 mg (2 equiv, 0.72 mmol) of 4-butylphenyl boronic acid to give 22.2 mg (18.3%) of methyl 4-[(4-butylphenyl)amino]-5-methylthiothiophene-2-carboxylate. 1H NMR (CDCl3, 400 MHz) δ0.97 (t, 2H, J=7.4 Hz), 1.38 (m, 2H), 1.59 (m, 2H obscured by water), 2.39 (s, 3H), 2.58 (t, 2H, J=7.6 Hz), 3.90 (s, 3H), 6.12 (bs, 1H), 6.97 (d, 2H, J=8.2 Hz), 7.12 (d, 2H, J=8.4 Hz), 7.73 (s, 1H).

Sources & evidence

ORD record
ord-ed9994d0127349458f85d297455ae10f
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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