3-Butyn-1-OL → HCID 59191301, compound

HRID 1023987Notes

Reaction equation

HRID 1023987 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[F:18])=[C:4]([O:19][CH3:20])[CH:3]=1.C(O)CC#C.[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)#[CH:27]>>[F:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[CH:6]=[CH:7][C:2]([C:27]#[C:26][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[CH:3][C:4]=1[O:19][CH3:20]

Participants

4

Reactant 3

HCID 135663-Butyn-1-OLHCID 137268EthynylpyridineHCID 59191251HCID 59191251, compound

Product 1

HCID 59191301HCID 59191301, compound

Procedure

According to the procedure of example 11(a) except substituting 5-bromo-2-(2-methoxy-4-propylphenoxy)pyridine by 4-bromo-1-(2-fluoro-4-nitrophenoxy)-2-methoxybenzene (0.29 mmol; 100 mg) and 3-butyn-1-ol by 2-ethynylpyridine (0.73 mmol; 73 μL), the title compound was prepared as a yellow solid (81%; 87 mg) after purification on preparative TLC (cyclohexane/ethyl acetate: 7/3).

Workup

  1. customafter purification on preparative TLC (cyclohexane/ethyl acetate: 7/3)

Sources & evidence

ORD record
ord-f900ad5b2fea474c9d2addad73a1122c
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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