Sodium Bicarbonate → HCID 53361079, compound

HRID 1023374Notes

Reaction equation

HRID 1023374 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:25]=[CH:26]/[C:27]([N:29]2[CH2:34][CH2:33][NH:32][C@@H:31]([CH3:35])[CH2:30]2)=[O:28])[CH:5]=[C:6]([CH3:24])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[CH:11][N:10]=1.[F:36][C:37]1[CH:53]=[CH:52][C:40]([O:41][CH2:42][CH2:43][C:44]2[CH:51]=[CH:50][C:47]([CH:48]=O)=[CH:46][CH:45]=2)=[CH:39][CH:38]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:25]=[CH:26]/[C:27]([N:29]2[CH2:34][CH2:33][N:32]([CH2:48][C:47]3[CH:50]=[CH:51][C:44]([CH2:43][CH2:42][O:41][C:40]4[CH:39]=[CH:38][C:37]([F:36])=[CH:53][CH:52]=4)=[CH:45][CH:46]=3)[C@@H:31]([CH3:35])[CH2:30]2)=[O:28])[CH:5]=[C:6]([CH3:24])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86673380HCID 86673380, compoundHCID 86673401HCID 86673401, compound

Product 1

HCID 53361079HCID 53361079, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 (5 mL) solution of (E)-3-[3-chloro-5-methyl-4-({5-[(4-methylbenzyl)oxy]pyridin-2-yl}oxy)phenyl]-1-[(3S)-3-methylpiperazin-1-yl]prop-2-en-1-one (0.50 g) and 4-[2-(4-fluorophenoxy)ethyl]benzaldehyde (298 mg) was added NaBH(OAc)3 (323 mg) at room temperature. The resultant mixture was stirred at room temperature for 3 days. To the reaction mixture was added saturated aqueous NaHCO3, and extracted with CH2Cl2. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1 to 0/1) to give (E)-3-[3-chloro-5-methyl-4-({5-[(4-methylbenzyl)oxy]pyridin-2-yl}oxy)phenyl]-1-[(3S)-4-{4-[2-(4-fluorophenoxy)ethyl]benzyl}-3-methylpiperazin-1-yl]prop-2-en-1-one as a yellow powder (451 mg).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1 to 0/1)

Sources & evidence

ORD record
ord-9794920478184156a5a5c747562ebf72
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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