o-Fluorobenzaldehyde → HCID 66614832, compound

HRID 1842056Notes

Reaction equation

HRID 1842056 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH:3]([C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[C:13]3[C:19]([O:21][CH3:22])=[O:20])=[O:8])[CH2:2]1.[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH:26]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Na]>C(O)(=O)C.ClCCl>[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][N:1]1[CH2:6][CH2:5][S:4][CH:3]([C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[C:13]3[C:19]([O:21][CH3:22])=[O:20])=[O:8])[CH2:2]1

Participants

7

Reactant 4

HCID 67970o-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 5360545SodiumHCID 66634445HCID 66634445, compound

Product 1

HCID 66614832HCID 66614832, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flask, dichloromethane (5 mL) and acetic acid (3 drops) was added to methyl 5-(thiomorpholine-2-carboxamido)-1H-indazole-3-carboxylate (0.320 g, 1 mmol) and 2-fluorobenzaldehyde (0.248 g, 2 mmol). The reaction was stirred for 15 minutes. Sodium triacetoxyborohydride (0.636 g, 3 mmol) was added in one portion. The reaction was stirred for an additional 16 hours. Saturated sodium bicarbarbonate (20 mL) was added. The reaction was stirred for an additional 5 minutes and was extracted with dichloromethane (30×1 mL). The extracts were combined, dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by flash column chromatography to give 250 mg product. LC-MS: 429.1.2 [M+H].

Workup

  1. stirringThe reaction was stirred for an additional 16 hours
  2. stirringThe reaction was stirred for an additional 5 minutes
  3. extractionwas extracted with dichloromethane (30×1 mL)
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-afe0ce099761412ebff27b6f9f39062d
Source dataset
uspto-grants-2015_02
Patent number
US08946216B2

Reaction notes

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