Diisopropylethylamine → 2-(2-Bromo-4-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047887Notes

Reaction equation

HRID 1047887 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([O:14][C:15]([C:17]1([NH2:26])[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1)=[O:16])[CH3:13].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:12]([O:14][C:15]([C:17]1([NH:26][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:2]=2[Br:1])[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1)=[O:16])[CH3:13]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2262922-Bromo-4-methylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10921653Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 593141512-(2-Bromo-4-methyl-benzoylamino)-indan-2-carboxylic acid ethyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-4-methyl-benzoic acid (314 mg, 1.46 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (300 mg, 1.46 mmol), HATU (666 mg, 1.75 mmol) in anhydrous DMF (1.8 mL) is added DIPEA (381 μL, 2.19 mmol). The resulting solution is stirred at RT overnight. Poured reaction into water (10 mL) and extracted with EtOAc (3×5 mL). The combined organic layers and concentrated in vacuo. The residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0-30% EtOAc in heptane) to give product (276) as off-white solid (445 mg, 76%).

Workup

  1. additionPoured
  2. extractionextracted with EtOAc (3×5 mL)
  3. concentrationThe combined organic layers and concentrated in vacuo
  4. customThe residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0-30% EtOAc in heptane)

Sources & evidence

ORD record
ord-91d45f760fed431cb70cd3500df63914
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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