Acetic Acid → HCID 59809528, compound

HRID 2114505Notes

Reaction equation

HRID 2114505 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:7]3[C:12]([S:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[CH:22]1[CH:27]=[C:26]([CH:28]=O)[N:25]=[CH:24][CH:23]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:16]3[CH2:21][CH2:20][N:19]([CH2:28][C:26]4[CH:27]=[CH:22][CH:23]=[CH:24][N:25]=4)[CH2:18][CH2:17]3)[C:7]3[C:12]([S:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 142732-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11516034HCID 11516034, compound2×

Product 1

HCID 59809528HCID 59809528, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-bromo-10-piperidin-4-yl-10H-phenothiazine, 5e (10.5 mg; 0.029 mmol) and 2-pyridyl carboxaldehyde (9.3 mg; 0.087 mmol) in dichloroethane (120 μL) was added acetic acid (5 μL) and a solution of sodium triacetoxyborohydride (12 mg, 0.057 mmol) in DMF (100 μL). The mixture was stirred at rt for 18 h, quenched with water (50 μL), and lyophilized. The thus obtained crude 3-bromo-10-(1-pyridin-2-ylmethyl-piperidin-4-yl)-10H-phenothiazine, 1f was used as such for the next reaction.

Workup

  1. customquenched with water (50 μL)

Sources & evidence

ORD record
ord-5d9e25610cc94d8a84c241972a924c04
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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