Sodium hydride → HCID 87135569, compound

HRID 1642406Notes

Reaction equation

HRID 1642406 reaction equation
[Cl-].[O:2]=[C:3]1[N:8]2[C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][S:11][C:7]2=[N:6][C:5]([CH2:16][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4]1.[H-].[Na+].CO[CH2:40][C:41]([CH3:53])([CH3:52])[CH2:42][O:43][C:44]1[CH:51]=[CH:50][CH:49]=[CH:48][C:45]=1[CH:46]=O.C1([CH2:57][O:58]C2C(OC)=CC=CC=2/C=C/C2N=C3SC=CN3C(=O)C=2I)CC1>CS(C)=O>[CH3:57][O:58][C:51]1[C:44]([O:43][CH2:42][C:41]([CH3:40])([CH3:52])[CH3:53])=[C:45](/[CH:46]=[CH:16]/[C:5]2[N:6]=[C:7]3[S:11][CH:10]=[C:9]([C:12]([F:13])([F:14])[F:15])[N:8]3[C:3](=[O:2])[CH:4]=2)[CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 66753592HCID 66753592, compoundHCID 87135560HCID 87135560, compoundHCID 87135686HCID 87135686, compound

Product 1

HCID 87135569HCID 87135569, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A stirred suspension of Step 3 intermediate (1.0 g, 1.886 mmol) in dry DMSO (10 ml) was treated with NaH (83 mg, 2.075 mmol) and 3-methoxy-2,2-dimethylpropoxy-benzaldehyde (460 mg, 2.075 mmol) according to the procedure described in Step 3, Intermediate 2 to yield a crude solid which was purified by column chromatography using 10% ethyl acetate in petroleum ether to afford 300 mg of the desired compound: 1H NMR (300 MHz, DMSO-d6) δ 1.08 (s, 9H), 3.56 (s, 2H), 3.79 (s, 3H), 6.13 (s, 1H), 7.02-7.18 (m, 3H), 7.32-7.35 (m, 1H), 8.15 (d, J=15.6 Hz 1H), 8.25 (s, 1H); ESI-MS (m/z) 439.11 (M+H)+.

Workup

  1. customto yield a crude solid which
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c44eb2c5950847e990acb00acd366a93
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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