Dichloromethane → HCID 136364222, compound

HRID 650424Notes

Reaction equation

HRID 650424 reaction equation
[Zn+2:1].[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:4]=1[C:10]1[C:11]2[NH:15][C:14]([C:16]([C:50]3[CH:55]=[CH:54][C:53]([C:56]#[C:57][Si](C)(C)C)=[CH:52][CH:51]=3)=[C:17]3[N:49]=[C:20]([C:21]([C:41]4[C:46]([F:47])=[CH:45][CH:44]=[CH:43][C:42]=4[F:48])=[C:22]4[NH:40][C:25](=[C:26]([C:32]5[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=5[F:39])[C:27]5[CH:28]=[CH:29][C:30]=1[N:31]=5)[CH:24]=[CH:23]4)[CH:19]=[CH:18]3)=[CH:13][CH:12]=2.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>C1COCC1.CO>[Zn+2:1].[C:56]([C:53]1[CH:54]=[CH:55][C:50]([C:16]2[C:17]3[NH:49][C:20](=[CH:19][CH:18]=3)[C:21]([C:41]3[C:42]([F:48])=[CH:43][CH:44]=[CH:45][C:46]=3[F:47])=[C:22]3[N:40]=[C:25]([CH:24]=[CH:23]3)[C:26]([C:32]3[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=3[F:39])=[C:27]3[NH:31][C:30]([CH:29]=[CH:28]3)=[C:10]([C:4]3[C:5]([F:9])=[CH:6][CH:7]=[CH:8][C:3]=3[F:2])[C:11]3=[N:15][C:14]=2[CH:13]=[CH:12]3)=[CH:51][CH:52]=1)#[CH:57]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 136364223HCID 136364223, compound

Product 1

HCID 136364222HCID 136364222, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Zn-3 (82 mg, 93.2 μmol) in THF (9 mL) was added a suspension of K2CO3 (30 mg, 217 μmol) in methanol (3 mL). The mixture was stirred for 1 h at room temperature in the dark. Then CH2Cl2 (20 mL) was added. The mixture was washed with aqueous 5% NaHCO3 solution (20 niL) and dried (Na2SO4). Purification by column chromatography (silica, CH2Cl2/hexanes 1:2) afforded 58 mg (71.6 μmol, 77%) of the title compound as a red-purple solid.

Workup

  1. washThe mixture was washed with aqueous 5% NaHCO3 solution (20 niL)
  2. dry with materialdried (Na2SO4)
  3. customPurification by column chromatography (silica, CH2Cl2/hexanes 1:2)

Sources & evidence

ORD record
ord-92858b792bc6403c8e0555214ac51d96
Source dataset
uspto-grants-2001_08
Patent number
US06272038B1

Reaction notes

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