Dichloromethane → HCID 67227831, compound

HRID 1515609Notes

Reaction equation

HRID 1515609 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.ClCCl.[C:26]1([S:32]([N:35]2[C:39]3=[N:40][CH:41]=[C:42]([CH:44]4[CH2:48][O:47][C:46]([CH3:50])([CH3:49])[O:45]4)[CH:43]=[C:38]3[CH:37]=[C:36]2[CH:51]([OH:58])[CH2:52][CH:53]2[CH2:57][CH2:56][CH2:55][CH2:54]2)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:26]1([S:32]([N:35]2[C:39]3=[N:40][CH:41]=[C:42]([CH:44]4[CH2:48][O:47][C:46]([CH3:49])([CH3:50])[O:45]4)[CH:43]=[C:38]3[CH:37]=[C:36]2[C:51](=[O:58])[CH2:52][CH:53]2[CH2:57][CH2:56][CH2:55][CH2:54]2)(=[O:34])=[O:33])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 67229482HCID 67229482, compound

Product 1

HCID 67227831HCID 67227831, compoundYield 106.2%

Procedure

A Dess-Martin periodinane solution in dichloromethane (0.3 M, 35 mL, 10.5 mmol) was added to 1-[1-benzenesulfonyl-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanol (1.7 g, 4.62 mmol) at 25° C. and then stirred for 1 h. The reaction was quenched with saturated aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate, washed with a saturated aqueous sodium bicarbonate (3×30 mL), brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 1-[1-benzenesulfonyl-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanone (2.3 g crude) as a light yellow solid which was used in the next step without further purification: LC/MS m/e calcd for C25H28N2O5S [M+H]+ 469.58, observed 469.2; 1H NMR (400 MHz, CDCl3) δ ppm 1.26 (m, 2H), 1.57-1.73 (m, 4H), 1.52 (s, 3H), 1.59 (s, 3H), 1.96 (m, 2H), 2.44 (m, 1 H), 3.03 (d, J=7.2 Hz, 2H), 3.74 (dd, J=7.6 Hz, 8.4 Hz, 1H), 4.39 (dd, J=6.4 Hz, 8.4 Hz, 1H), 5.19 (dd, J=6.4 Hz, 7.6 Hz, 1H), 6.94 (s, 1H), 7.55 (m, 2H), 7.62 (m, 1H), 7.93 (d, J=2.0 Hz, 1H), 8.39 (d, J=7.6 Hz, 2H), 8.56 (d, J=2.0 Hz, 1H).

Workup

  1. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with a saturated aqueous sodium bicarbonate (3×30 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd3fe556f8e94e288f826075a61e644a
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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