Acetic Anhydride → HCID 9943807, compound

HRID 1761025Notes

Reaction equation

HRID 1761025 reaction equation
[N:1]1([C:4]2[C:5](=[O:18])[C:6]3[C:7]([CH3:17])=[C:8]([CH2:15][OH:16])[NH:9][C:10]=3[C:11](=[O:14])[C:12]=2[CH3:13])[CH2:3][CH2:2]1.CN(C1C=CC=CN=1)C.[C:28](OC(=O)C)(=[O:30])[CH3:29].[K+].[Br-]>C(Cl)(Cl)Cl.C(Cl)(Cl)Cl.CO>[C:28]([O:16][CH2:15][C:8]1[NH:9][C:10]2[C:11](=[O:14])[C:12]([CH3:13])=[C:4]([N:1]3[CH2:3][CH2:2]3)[C:5](=[O:18])[C:6]=2[C:7]=1[CH3:17])(=[O:30])[CH3:29]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 253877Potassium BromideHCID 9813608HCID 9813608, compound

Product 1

HCID 9943807HCID 9943807, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 21584188Chloroform methanolSolvent

Procedure

To a mixture of 10 mg of indole 1b (0.04 mmole), 5 mg (0.04 mmole) dimethylaminopyridine (DMAP) in 5 ml of chloroform, was added 100 mg of acetic anhydride. The reaction was stirred at room temperature for 25 min and then added directly to a silica gel chromatography column employing chloroform as the eluant. The purified indole 1c was recrystallized from chloroform/hexane: 11 mg (95%) yield; mp 210-212° C.; TLC (chloroform/methanol, 90:10) Rf=0.68; 1HNMR (CDCl3) δ 9.38 (1H, bs, indole proton), 5.03 (2H, s, 2-methylene), 2.32 (4H, s, ethylene), 2.31 (3H, s, 3-methyl) 2.08 and 2.05 (6H, 2s, methyls); IR (KBr pellet) 3207, 2924, 1734, 1664, 1624, 1566, 1500, 1361, 1350, 1242, 1209, 1155, 1020, 962, 817, 781 cm−1; MS (EI mode) m/z 288 (M+), 245 (M+-CH3—C═O), 228, 213, 201, 185. Anal. Calcd (C15H16N2O4) C, H, N.

Workup

  1. additionadded directly to a silica gel chromatography column
  2. customThe purified indole 1c was recrystallized from chloroform/hexane
  3. custom11 mg (95%) yield

Sources & evidence

ORD record
ord-bd82b461c2334a0cae8cf26d90a6ae0a
Source dataset
uspto-grants-2005_01
Patent number
US06846840B2

Reaction notes

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