4-Chlorophenyl trifluoromethanesulphonate → 2-[4-(5-Chloropyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole

HRID 7784

Reaction equation

HRID 7784 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:10][C:9]=2[O:23][CH3:24])[CH:5]=[CH:4][CH:3]=1.COC1C=C(C2OC3C=CC=CC=3N=2)C=CC=1B1OC(C)(C)C(C)(C)O1.FC(F)(F)S(OC1C=CC([Cl:63])=CC=1)(=O)=O>>[Cl:63][C:3]1[CH:4]=[CH:5][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:10][C:9]=2[O:23][CH3:24])=[N:7][CH:2]=1

Participants

4

Reactant 3

HCID 5814244-Chlorophenyl trifluoromethanesulphonateHCID 103093892-[4-(6-Bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazoleHCID 219909862-[3-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole

Product 1

HCID 103087512-[4-(5-Chloropyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole

Procedure

Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (100 mg, 0.28 mmol) was reacted with 4-chlorophenyl trifluoromethanesulfonate (74 mg, 0.28 mmol) to afford the desired 2-[4-(5-chloropyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.69–8.68 (d, 1H), 7.98 (s, 2H), 7.94–7.90 (m, 2H), 7.86–7.78 (m, 1H), 7.74–7.73 (m, 1H), 7.65–7.58 (m, 1H), 7.40–7.37 (m, 2H), 4.03 (s, 3H). MS (ESI) 337 (M+H)+.

Sources & evidence

ORD record
ord-e4addf6843844e34bf17ccec7031bdb4
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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