1,1'-Carbonyldiimidazole → HCID 69058821, compound

HRID 1984301Notes

Reaction equation

HRID 1984301 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.[C:13]([O:17][C:18](=[O:26])[N:19]([CH3:25])[CH:20]1[CH2:24][CH2:23][NH:22][CH2:21]1)([CH3:16])([CH3:15])[CH3:14].C1N=CN(C(N2C=NC=C2)=O)C=1>C1COCC1>[C:13]([O:17][C:18](=[O:26])[N:19]([CH:20]1[CH2:24][CH2:23][N:22]([C:10]([C:2]2[NH:1][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:12])[CH2:21]1)[CH3:25])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 72899Indole-2-carboxylic acidHCID 27614043-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidine

Product 1

HCID 69058821HCID 69058821, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of indole-2-carboxylic acid (388 mg, 2.40 mmol) and methyl-pyrrolidin-3-yl-carbamic acid tert-butyl ester (401 mg, 2.00 mmol) in THF (16 mL) was added CDI (356 mg, 2.20 mmol). After 18 h at rt, the mixture was concentrated, diluted with CH2Cl2, washed with satd. aq. Na2CO3 and water, dried (Na2SO4), and concentrated. The residue was purified by FCC to give the title compound (565 mg, 69%). MS (ESI): mass calcd. for C19H25N3O3, 343.19; m/z found, 344 [M+H]+. 1H NMR (CDCl3): 9.73 (s, 1H), 7.67 (d, J=8.0, 1H), 7.46 (dd, J=8.3, 0.8, 1H), 7.29 (t, J=8.2, 1H), 6.89 (d, J=1.3, 1H), 4.89 (br s, 1H), 4.26-3.49 (m, 4H), 2.85 (s, 3H), 2.36-1.96 (m, 2H), 1.76 (s, 1H), 1.49 (s, 9H). Anal. Calcd for C19H25N3O3: C, 66.45; H, 7.34; N, 12.24. Found: C, 66.42; H, 7.55; N, 12.10.

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with CH2Cl2
  3. washwashed with satd
  4. dry with materialaq. Na2CO3 and water, dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-92ebb604d2af42e69431bcc639531a26
Source dataset
uspto-grants-2009_06
Patent number
US07544698B2

Reaction notes

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