Chloroacetaldehyde → 6-Bromo-7-methyl-8-(3-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

HRID 1497758Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.Cl[CH2:21][CH:22]=O>>[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[CH:10]=2)[C:5]2[N:6]([CH:21]=[CH:22][N:8]=2)[CH:7]=1

Participants

Reactant 2

HCID 33Chloroacetaldehyde

HCID 867080865-Bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-ylamine

Product 1

HCID 867080956-Bromo-7-methyl-8-(3-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

Procedure

The title compound was prepared from 5-bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-ylamine (Int. 1, 237 mg, 0.716 mmol), using a similar method to that used in Example 5 (Step 1) and replacing 1-chloropropan-2-one with 2-chloroacetaldehyde (185 μL, 1.43 mmol) (233 mg).

Sources & evidence

ORD record: ord-b79068fbc09e4f2dbbb0a85159df73fc
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199984B2

Reaction notes

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