2-Methyl-2-butene → HCID 68672018, compound

HRID 1186595Notes

Reaction equation

HRID 1186595 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:46]=[C:47]([F:49])[CH:48]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[N:10]=[C:9]2[NH:34][C:35](=[O:45])[C:36]1[CH:41]=[C:40]([CH:42]=[O:43])[CH:39]=[CH:38][C:37]=1[F:44].CC(=CC)C.Cl([O-])=[O:56].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:46]=[C:47]([F:49])[CH:48]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[N:10]=[C:9]2[NH:34][C:35](=[O:45])[C:36]1[CH:41]=[C:40]([CH:39]=[CH:38][C:37]=1[F:44])[C:42]([OH:56])=[O:43]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86647620HCID 86647620, compound

Product 1

HCID 68672018HCID 68672018, compoundYield 117.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[5-(3,5-Difluoro-benzyl)-1-trityl-1H-indazol-3-yl]-2-fluoro-5-formyl-benzamide (88 mg, 0.135 mmol) in tert-butanol (1.8 mL) at room temperature was treated first with 2-methyl-2-butene (0.079 mL, 1.082 mmol) and then with sodium chlorite (37 mg, 0.405 mmol) and sodium dihydrogenphosphate in water (0.8 mL) drop-wise. The reaction was stirred over-night, EtOAc was then added (30 mL) and washed with water (25 mL). The aqueous layer was extracted twice with EtOAc (2×10 mL). The combined organic layers were washed with brine, evaporated to dryness to leave 106 mg of title compound which was employed in the following step with no need of further purification.

Workup

  1. washwashed with water (25 mL)
  2. extractionThe aqueous layer was extracted twice with EtOAc (2×10 mL)
  3. washThe combined organic layers were washed with brine
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-c0eb35d19bea474bbb2882e93da269f7
Source dataset
uspto-grants-2014_03
Patent number
US08673893B2

Reaction notes

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