4-Bromo-2-fluorobenzaldehyde → 2-(4-Bromo-2-fluorophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

HRID 1177561Notes

Reaction equation

HRID 1177561 reaction equation
[NH2:1][C:2]1[C:3](=[S:17])[NH:4][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[C:21]([F:27])[CH:20]=1.NC1C(=S)NC=CC=1>>[Br:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]2[S:17][C:3]3[C:2]([N:1]=2)=[CH:7][CH:6]=[C:5]([C:8]2([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:10][CH2:9]2)[N:4]=3)=[C:21]([F:27])[CH:20]=1

Participants

4

Reactant 3

HCID 1435174-Bromo-2-fluorobenzaldehydeHCID 54631813-Aminopyridine-2-thiolHCID 591748363-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione

Product 1

HCID 671119992-(4-Bromo-2-fluorophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

Procedure

Reaction of 3-amino-6-(1-phenylcyclopropyl)pyridine-2(1H)-thione (50.0 mg, 206 μmol) and 4-bromo-2-fluorobenzaldehyde (44.0 mg, 217 μmol) according to Reference U and the general procedure for oxidative condensation of 3-aminopyridine-2-thione with aryl aldehydes gave 2-(4-bromo-2-fluorophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine as a light yellow solid. MS (ESI) m/z: Calculated: 424.0; Observed: 424.9 (M++1).

Sources & evidence

ORD record
ord-9cb93cc2bc0d422e912b6bad67240fc1
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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