Diethyl Ether → 1-(Benzenesulfonyl)-4-chloro-1H-pyrrolo[2,3-b]pyridine

HRID 1257573Notes

Reaction equation

HRID 1257573 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][N:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C(N(CC)CC)C.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(OCC)C>ClCCl.CN(C)C1C=CN=CC=1>[C:18]1([S:24]([N:6]2[C:7]3=[N:8][CH:9]=[CH:10][C:2]([Cl:1])=[C:3]3[CH:4]=[CH:5]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 50602241-(Benzenesulfonyl)-4-chloro-1H-pyrrolo[2,3-b]pyridineYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A stirred suspension of 4-chloro-7-azaindole (1.00 g, 6.55 mmol) in dichloromethane (DCM) (50 ml) was treated with 4-(dimethylamino)pyridine (80.0 mg, 0.66 mmol), triethylamine (1.36 ml, 9.83 mmol) and benzenesulfonyl chloride (0.93 ml, 7.21 mmol) at ambient temperature. The mixture was left to stand overnight and then diluted with DCM and washed with 1M aqueous HCl solution, saturated sodium hydrogen carbonate solution, water, and brine, dried with sodium sulfate and concentrated under vacuum to give crude product. Trituration (diethyl ether) afforded 1.59 g (83%) of 1-benzenesulfonyl-4-chloro-1H-pyrrolo[2,3-b]pyridine. LCMS (Method B, ESI): RT=4.48 min, m+H=293.3; 1H NMR (400 MHz, CDCl3) δ: 8.31 (d, 1H), 8.18 (m, 2H), 7.78 (m, 1H), 7.62-7.56 (m, 1H), 7.52-7.45 (m, 2H), 7.20 (m, 1H), 6.72 (m, 1H).

Workup

  1. waitThe mixture was left
  2. washwashed with 1M aqueous HCl solution, saturated sodium hydrogen carbonate solution, water, and brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give crude product

Sources & evidence

ORD record
ord-360f688ff71f4a3bab20ae6fe1b854a9
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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