Acetic Acid → Ethyl 2-{(E)-2-[3-(difluoromethoxy)-2-hydroxyphenyl]vinyl}imidazo[1,2-a]pyridine-3-carboxylate

HRID 1882145Notes

Reaction equation

HRID 1882145 reaction equation
Br.[F:2][CH:3]([F:27])[O:4][C:5]1[C:6]([OH:26])=[C:7](/[CH:11]=[CH:12]/[C:13]2[N:14]=[C:15]3[N:19]([C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:18]=[CH:17]S3)[CH:8]=[CH:9][CH:10]=1.[CH3:28][C:29](O)=O>>[F:2][CH:3]([F:27])[O:4][C:5]1[C:6]([OH:26])=[C:7](/[CH:11]=[CH:12]/[C:13]2[N:14]=[C:15]3[CH:29]=[CH:28][CH:17]=[CH:18][N:19]3[C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 59369921Ethyl 6-{(E)-2-[3-(difluoromethoxy)-2-hydroxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylate

Product 1

HCID 59369912Ethyl 2-{(E)-2-[3-(difluoromethoxy)-2-hydroxyphenyl]vinyl}imidazo[1,2-a]pyridine-3-carboxylate

Procedure

The Step 1 intermediate (4.3 g, 9.674 mmol) was treated with 48% hydrobromic acid (20 mL) in glacial AcOH (20 mL) as described in Intermediate 6 gave 3.1 g of the product as white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.44 (t, J=7.2 Hz, 3H), 4.44 (q, J=7.2 Hz, 2H), 6.92 (d, J=7.8 Hz, 1H), 7.12 (t, J=74.1 Hz, 1H), 7.15-7.22 (m, 2H), 7.48 (d, J=7.8 Hz, 1H), 7.57 (t, J=7.8 Hz, 1H), 7.75 (d, J=9.3 Hz, 1H), 7.95 (d, J=16.2 Hz, 1H), 8.08 (d, J=15.9 Hz, 1H), 9.24 (d, J=6.9 Hz, 1H), 9.83 (br, 1H); APCI-MS (m/z) 375.16 (MH)+.

Sources & evidence

ORD record
ord-864ddb7e220748eb98fd33f1355a702c
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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