Chlorosuccinimide → 6-Bromo-3-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine

HRID 2205897Notes

Reaction equation

HRID 2205897 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.[Br:9][C:10]1[N:15]=[CH:14][C:13]2[CH:16]=[C:17]([C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)[NH:18][C:12]=2[CH:11]=1>CN(C=O)C>[Br:9][C:10]1[N:15]=[CH:14][C:13]2[C:16]([Cl:8])=[C:17]([C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)[NH:18][C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 867062766-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 867063076-Bromo-3-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridineYield 76.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NCS (48 mg, 0.361 mmol) was added to a solution of 6-bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 100 mg, 0.361 mmol) in DMF (1.1 mL). The reaction mixture was stirred overnight at room temperature before being filtered on an SCX-2 column and concentrated under vacuum. The residue was purified via Biotage silica gel column chromatography eluting with (DCM/EtOH 99/1 to 95/5) to afford the title product as a white solid (86 mg, 76%). 1H NMR (500 MHz, CD3OD) δ 4.01 (s, 3H), 7.54 (d, J=0.8 Hz, 1H), 8.05 (s, 1H), 8.28 (s, 1H), 8.47 (d, J=0.8 Hz, 1H). LC (Method B)-MS (ESI, m/z) tR 2.84 min, 312 [(M+H+), 100%].

Workup

  1. filtrationbefore being filtered on an SCX-2 column
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified via Biotage silica gel column chromatography
  4. washeluting with (DCM/EtOH 99/1 to 95/5)

Sources & evidence

ORD record
ord-190c4e81cfb446ca9f8ba69e34b095ef
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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