Propargyl bromide → HCID 131732833, compound

HRID 2272732Notes

Reaction equation

HRID 2272732 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[N:16]=[CH:15][CH:14]=[C:13]2[O:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([C:32]2[C:33](=[O:46])[N:34]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[C:35](=[O:38])[NH:36][N:37]=2)=[O:31])=[CH:25][C:24]=1[F:47].[CH2:48](Br)[C:49]#[CH:50].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:3][C:2]([C:4]([F:7])([F:6])[F:5])=[O:1].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[N:16]=[CH:15][CH:14]=[C:13]2[O:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([C:32]2[C:33](=[O:46])[N:34]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[C:35](=[O:38])[N:36]([CH2:50][C:49]#[CH:48])[N:37]=2)=[O:31])=[CH:25][C:24]=1[F:47]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 131732834HCID 131732834, compound

Product 1

HCID 131732833HCID 131732833, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of example 107 (25 mg, 0.046 mmol), propargyl bromide (10 uL, 0.1 mmol), and potassium carbonate (10 mg, 0.07 mmol) in N,N-dimethylformamide (1 mL) was stirred at rt 18 h. The mixture was filtered, solvent was removed and the product was purified by reverse phase HPLC to give an off-white solid (7 mg, 30%). LCMS m/z=586 (M+1); 1H NMR (DMSO) δ: 10.99 (s, 1H), 8.71 (d, 1H, J=6.1 Hz), 8.0 (dd, 1H, J=2.3, 12.7 Hz), 7.68 (s, 1H), 7.65-7.58 (m, 2H), 7.4 (s, 1H), 7.37-7.35 (m, 4H), 6.84 (d, 1H, J=5.8 Hz), 4.88 (d, 2H, J=2.3 Hz), 4.01 (2 s, 6H), 3.53 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customsolvent was removed
  3. customthe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-3e4bb691dce54dfab9070fcfe31b68ce
Source dataset
uspto-grants-2015_09
Patent number
US09120778B2

Reaction notes

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