2-Bromopyridine → HCID 11680534, compound

HRID 1189096Notes

Reaction equation

HRID 1189096 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([C:12]1[O:13][C:14]2[C:15](=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=2)[N:16]=1)[CH2:9][C:10]#[CH:11]>>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]#[C:10][CH2:9][CH2:8][C:12]1[O:13][C:14]2[C:15](=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=2)[N:16]=1

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 86086730HCID 86086730, compound

Product 1

HCID 11680534HCID 11680534, compoundYield 7,364.3%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromopyridine (203 mg, 1.29 mol) and 2-(but-3-ynyl)benzo[d]oxazol-4-ol (241 mg, 1.29 mmol). The crude residue was purified by flash chromatography (DCM/MeOH 99:1 to 98:2) and SCX column (DCM/MeOH 100:0 to 94:6, DCM/MeOH/NH4OH 94:5:1 to 90:8:2) to yield 25 mg (95 mmol, 7%) of 2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazol-4-ol as an orange solid.

Workup

  1. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1 to 98:2) and SCX column (DCM/MeOH 100:0 to 94:6, DCM/MeOH/NH4OH 94:5:1 to 90:8:2)

Sources & evidence

ORD record
ord-6267a7e4005f4719b7a78ec6dae8723c
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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