P-Anisidine → HCID 78321754, compound

HRID 1775648Notes

Reaction equation

HRID 1775648 reaction equation
[C:1]1([N:7]2[C:12](=[O:13])[C:11]3[S:14][CH:15]=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:10]=3[N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC1C(C2C=CC=CC=2[Br:35])=CSC=1C(OC)=O.C([O:47][CH2:48]C)(OCC)OCC.COC1C=CC(N)=CC=1>C(O)(=O)C>[Br:35][C:22]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:16]1[C:10]2[N:9]=[CH:8][N:7]([C:1]3[CH:6]=[CH:5][C:4]([O:47][CH3:48])=[CH:3][CH:2]=3)[C:12](=[O:13])[C:11]=2[S:14][CH:15]=1

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 31214Ethyl orthoformateHCID 783248653,7-Diphenylthieno[3,2-d]pyrimidin-4(3H)-oneHCID 86729803HCID 86729803, compound

Product 1

HCID 78321754HCID 78321754, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same manner as the synthesis of Compound 1, methyl 3-amino-4-(2-bromophenyl)thiophene-2-carboxylate (1.4 g, 4.48 mmol), triethyl orthoformate (12 ml), p-anisidine (930 mg, 8.52 mmol), and acetic acid (1.2 ml) were used to give 422 mg (1.02 mmol, 23% yield) of the title compound.

Sources & evidence

ORD record
ord-9654f3e226cc481589da59937c96d243
Source dataset
uspto-grants-2016_02
Patent number
US09260448B2

Reaction notes

Loading…