Trifluoroacetic acid → HCID 11472360, compound

HRID 1592963Notes

Reaction equation

HRID 1592963 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:11]=[C:12]([C:15]4([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[CH2:17][CH2:16]4)[S:13][CH:14]=3)=[CH:9][C:4]=2[O:3]C1.B(Br)(Br)Br.CO.O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:3][C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[C:12]([C:15]3([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:16][CH2:17]3)[S:13][CH:14]=2)[CH:7]=[CH:6][C:5]=1[OH:1]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 25134Boron tribromideHCID 22242641Methanol--water (1/1)HCID 58998535HCID 58998535, compound

Product 1

HCID 11472360HCID 11472360, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

4-(1,3-benzodioxol-5-yl)-2-(1-phenylcyclopropyl)-1,3-thiazole (3-1 [synthesized by the method described in Scheme 1], 0.04 g, 0.121 mmol) in methylene chloride (5.0 mL) was cooled to −78° C. and treated with BBr3 (1.0M solution in methylene chloride, 0.60 mL, 0.60 mmol). The reaction stirred 12 h at −78° C. and was subjected directly to reverse phase HPLC (C-8, 5-95% MeOH—H2O w/0.1% TFA) to provide pure 4-(3,4-dihydroxyphenyl)-2-(1-phenylcyclopropyl)-1,3-thiazole (3-2). 1H NMR (300 MHz, CDCl3) δ 7.48 (d, J=7.1 Hz, 2H), 7.39 (m, 3H), 7.51 (d, J=7.6 Hz, 2H), 7.14 (br s, 1H), 7.02 (s, 1H), 6.97 (d, J=7.9 Hz, 1H), 6.72 (d, J=7.9 Hz, 1H), 2.05 (m 2H), 1.70 (m, 2H); MS 309.9 found 310.4 (M+H+) required.

Sources & evidence

ORD record
ord-5d51ba968a0042e4b1f19c38b30804bf
Source dataset
uspto-grants-2007_11
Patent number
US07294640B2

Reaction notes

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