2-Cyanophenylboronic acid → 5-Amino-4-cyano-3-(2'-cyano-biphenyl-4-yl)-thiophene-2-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([NH2:27])=[C:9]([C:25]#[N:26])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2SC)=[CH:13][CH:12]=1)=[O:5])[CH3:2].C(OC(C1SC(N)=C([C:45]#[N:46])C=1C1C=CC(I)=CC=1)=O)C.C(C1C=CC=CC=1B(O)O)#N>>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([NH2:27])=[C:9]([C:25]#[N:26])[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:45]#[N:46])=[CH:15][CH:16]=1)=[O:5])[CH3:2]Participants
4
Reactant 3
Product 1
Procedure
Using a method substantially in accordance with the method of 5-amino-4-cyano-3-(2′methylsulfanyl-biphenyl-4-yl)-thiophene-2-carboxylic acid ethyl ester starting with the compound 5-amino-4-cyano-3(4-iodo-phenyl)-thiophene-2-carboxylic acid ethyl ester and 2-(cyano)phenylboronic acid gives the title compound: 1H NMR (400 MHz, CDCl3) δ 7.81-7.44 (m, 8H), 5.29 (s, 2H), 4.16 (q, 2H, J=7.2 Hz), 1.17 (t, 3H, J=7.3 Hz), MS found (M−1) 372.0 and (M+1)+NH3 391.0.
Sources & evidence
- ORD record
- ord-97bf9ddb4c314bfd888e167c09158726
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07642361B2
Reaction notes
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