Diisopropylethylamine → 3-Bromo-4-methyl-N-(4-(2-(pyrrolidin-1-yl)ethyl)phenyl)benzamide

HRID 2172675Notes

Reaction equation

HRID 2172675 reaction equation
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:14]([OH:16])=O.[N:21]1([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[Br:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:14]([NH:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][CH2:26][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:29][CH:30]=1)=[O:16]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 821303-Bromo-4-methylbenzoic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 64870474-(2-(Pyrrolidin-1-yl)ethyl)aniline

Product 1

HCID 684662633-Bromo-4-methyl-N-(4-(2-(pyrrolidin-1-yl)ethyl)phenyl)benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DIEA (4734, 2.72 mmol) was added into a solution of 3-bromo-4-methylbenzoic acid (189 mL, 0.881 mmol), 4-(2-(pyrrolidin-1-yl)ethyl)benzenamine (140 mg, 0.734 mmol), BOP (487 mg, 1.01 mmol) in DMF. The reaction mixture was stirred at rt under argon atmosphere overnight. The reaction mixture was diluted with AcOEt, and then washed with 1N NaOH aqueous solution three times. Organic phase was dried with anhydrous Na2SO4, and then evaporated to remove organic solvents. The obtained residue was further dried under high vacuum overnight to give crude product, which was used directly for the next step synthesis without further purification. MS (ESI+) m/z 387.0 [M+H]+.

Workup

  1. washwashed with 1N NaOH aqueous solution three times
  2. dry with materialOrganic phase was dried with anhydrous Na2SO4
  3. customevaporated
  4. customto remove organic solvents
  5. customThe obtained residue was further dried under high vacuum overnight
  6. customto give crude product, which
  7. customwas used directly for the next step synthesis without further purification

Sources & evidence

ORD record
ord-4f4bcc7068a748a9a90fb0bba525f25c
Source dataset
uspto-grants-2015_06
Patent number
US09056837B2

Reaction notes

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