HCID 21081810, compound → HCID 21081593, compound

HRID 2117187Notes

Reaction equation

HRID 2117187 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([N+:29]([O-])=O)[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[N:11](C(OC(C)(C)C)=O)[CH:12]=[C:13]([C:14]#[C:15][CH2:16][OH:17])[C:6]=12>C1COCC1.CO.[Pd]>[NH2:29][C:27]1[CH:26]=[CH:25][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[NH:11][CH:12]=[C:13]([CH2:14][CH2:15][CH2:16][OH:17])[C:6]=23)=[C:2]([F:1])[CH:28]=1

Participants

5

Reactant 1

HCID 21081810HCID 21081810, compound

Product 1

HCID 21081593HCID 21081593, compoundYield 13.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 4-(2-fluoro-4-nitrophenoxy)-3-(3-hydroxyprop-1-ynyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (50 mg, 0.15 mmol) and 10% Pd/C (containing 50% H2O, 120 mg) in THF (10 mL) and MeOH (2 mL) was hydrogenated at 1 atm for 5 h. The mixture was diluted with MeOH and filtered through a pad of Celite®. The crude mixture was purified by preparative HPLC to afford the desired product (6 mg, 13% yield) as a white solid. LC/MS (ESI+) m/z 302 (M+H)+.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. customThe crude mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-038a27a6888c42bf99687f957f16d35f
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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