Water → HCID 53252010, compound

HRID 2271372Notes

Reaction equation

HRID 2271372 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Br:15][C:16]1[CH:17]=[C:18]([NH2:22])[CH:19]=[N:20][CH:21]=1.[OH:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH:26]=O.O>ClCCl>[Br:15][C:16]1[CH:17]=[C:18]([NH:22][CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=2[OH:23])[CH:19]=[N:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6998Salicylaldehyde2×HCID 8176813-Amino-5-bromopyridine2×HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 53252010HCID 53252010, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

295 mg (1.4 mmol, 1.4 eq) of sodium triacetoxyborohydride are added to a solution of 173 mg (1 mmol, 1 eq) of 5-bromopyridin-3-ylamine (starting material 1) and 122 mg (1 mmol, 1 eq) of 2-hydroxybenzaldehyde (starting material 2) in 20 ml of dichloromethane. The solution is stirred at room temperature for 24 h. The medium is poured into water and stirred for 2 h. The aqueous phase is extracted with dichloromethane. The organic phases are combined, washed with water, and then dried over sodium sulphate. The residue is chromatographed on silica gel (80/20 heptane/ethyl acetate). 2-[(5-Bromopyridin-3-ylamino)methyl]phenol is obtained in the form of a white solid.

Workup

  1. stirringstirred for 2 h
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. customThe residue is chromatographed on silica gel (80/20 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-013ebbf024714e52a54e3598726f3ed5
Source dataset
uspto-grants-2015_09
Patent number
US09120753B2

Reaction notes

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