Bicarbonate Ion → HCID 67155794, compound

HRID 2196695Notes

Reaction equation

HRID 2196695 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:17][C:18](Br)([CH3:20])[CH3:19].C(=O)(O)[O-]>ClCCl>[C:18]([C:12]1[C:6]2[C:7](=[N:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:10][CH:11]=1)([CH3:20])([CH3:19])[CH3:17]

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 10485t-Butyl bromideHCID 6451240Aluminum(III) ChlorideHCID 115211405-Nitro-7-azaindole

Product 1

HCID 67155794HCID 67155794, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-Nitro-1H-pyrrolo[2,3-b]pyridine (150 mg, 0.92 mmol) was taken up in dry dichloromethane (9 mL) and was chilled to 0° C. Aluminum chloride (613 mg, 4.60 mmol, 5 eq.) was then added, and the mixture was allowed to stir at 0° C. for 15 minutes. 2-Methyl-2-bromopropane (107 μL, 0.919 mmol) was then added, and the mixture was allowed to gradually warm to room temperature over a 16 hour period. The mixture was then poured into cold saturated bicarbonate solution and extracted with dichloromethane (2×). The extracts were dried over sodium sulfate and concentrated. Prep plate purification (2×1.0 mm plates, 3:1 hexane:ethyl acetate) afforded 3-tert-butyl-5-nitro-1H-pyrrolo[2,3-b]pyridine (8.3 mg, 4%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 12.25 (br s, 1H), 9.07-9.09 (m, 1H), 8.84-8.86 (m, 1H), 7.48 (s, 1H), 1.42 (s, 9H); m/z (APCI-neg) M−1=218.3.

Workup

  1. temperatureto gradually warm to room temperature over a 16 hour period
  2. extractionextracted with dichloromethane (2×)
  3. dry with materialThe extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customPrep plate purification (2×1.0 mm plates, 3:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-606a9bb5e65d4fd9b2082523d785b9c3
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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