4-Fluorobenzaldehyde → HCID 178516040, compound

HRID 340044Notes

Reaction equation

HRID 340044 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:17]4[NH:18][C:19]5[CH2:24][CH2:23][NH:22][CH2:21][C:20]=5[N:25]=4)=[N:13][NH:14]3)=[CH:10][CH:9]=2)[C:5]([CH2:26][C:27]([F:30])([F:29])[F:28])=[CH:4][C:3]=1[OH:31].CC([O-])=O.[K+].[F:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=O)=[CH:40][CH:39]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:17]4[NH:18][C:19]5[CH2:24][CH2:23][N:22]([CH2:42][C:41]6[CH:44]=[CH:45][C:38]([F:37])=[CH:39][CH:40]=6)[CH2:21][C:20]=5[N:25]=4)=[N:13][NH:14]3)=[CH:10][CH:9]=2)[C:5]([CH2:26][C:27]([F:28])([F:29])[F:30])=[CH:4][C:3]=1[OH:31]

Participants

6

Reactant 4

HCID 680234-FluorobenzaldehydeHCID 517044Potassium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 1785160382-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-5-(2,2,2-trifluoro-ethyl)-phenol

Product 1

HCID 178516040HCID 178516040, compoundYield 30.35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-5-(2,2,2-trifluoro-ethyl)-phenol (Preparation 39, 100 mg, 0.21 mmol) and KOAc (22.75 mg, 0.23 mmol) in MeOH (1 mL), 4-fluorobenzaldehyde (57.54 mg, 0.46 mmol) was added and the mixture stirred at room temperature for 1 hr followed by portionwise addition of sodium triacetoxy borohydride (162.12 mg, 0.76 mmol) over 2 hrs. The mixture was thereafter stirred at room temperature for 18 hrs. The reaction mixture was concentrated and the residue partitioned between saturated sodium bicarbonate solution & ethyl acetate. The organic phase was dried over sodium sulphate, evaporated in vacuo, purified initially over silica and finally by Prep TLC (Mobile Phase: 10% MeOH-DCM) to afford the title compound as a light yellow solid in 30.35% yield, 35 mg.

Workup

  1. stirringThe mixture was thereafter stirred at room temperature for 18 hrs
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue partitioned between saturated sodium bicarbonate solution & ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated in vacuo
  6. custompurified initially over silica and finally by Prep TLC (Mobile Phase: 10% MeOH-DCM)

Sources & evidence

ORD record
ord-100663e3120b4c44a7c954c1b2007708
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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