Allyl bromide → HCID 22137844, compound

HRID 1827356Notes

Reaction equation

HRID 1827356 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14](O)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:23]([F:26])([F:25])[F:24].[CH2:27](Br)[CH:28]=[CH2:29].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([CH2:29][CH:28]=[CH2:27])[CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:23]([F:26])([F:25])[F:24]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 22137850HCID 22137850, compound

Product 1

HCID 22137844HCID 22137844, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The phenol compound obtained from Example 133 was treated with allyl bromide (1 eq.), and K2CO3 (2 eq.) in DMF at 60° C. for 24 h. After the reaction was finished, the resulting solution was directly injected on a preparative reverse phase HPLC column and fractions, which contained the desired product mass, were collected and concentrated using the Genevac system. 1H NMR (CD3OD) δ 7.98 (d, J=2 Hz, 1 H), 7.65 (dd, J=2 Hz, J=8 Hz, 1 H) 7.50 (d, J=8 Hz, 1 H), 7.38 (s, 1 H), 7.34 (s, 1 H), 6.86 (s, 1 H), 6.07 (m, 1 H), 5.42 (dq, J=2 Hz, J=17 Hz, 1 H), 5.29 (dq, J=2 Hz, J=12 Hz, 1 H), 4.61 (dt, J=2 Hz, J=5 Hz, 2 H).

Sources & evidence

ORD record
ord-722275019141429584c0c8a4e995a955
Source dataset
uspto-grants-2006_05
Patent number
US07053234B2

Reaction notes

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