Methoxymethyl-triphenylphosphonium chloride → HCID 67148474, compound

HRID 1786704Notes

Reaction equation

[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:24]([Li])CCC.[C:29]([O:33][C:34]([N:36]1[C:44]2[C:39](=[CH:40][CH:41]=[C:42](C=O)[CH:43]=2)[CH:38]=[C:37]1[C:47]1[CH:52]=[C:51]([C:53]2[CH:58]=[CH:57][N:56]=[CH:55][CH:54]=2)[N:50]=[N:49][C:48]=1[O:59][CH3:60])=[O:35])([CH3:32])([CH3:31])[CH3:30]>C1COCC1>[C:29]([O:33][C:34]([N:36]1[C:44]2[C:39](=[CH:40][CH:41]=[C:42]([CH:24]=[CH:4][O:3][CH3:2])[CH:43]=2)[CH:38]=[C:37]1[C:47]1[CH:52]=[C:51]([C:53]2[CH:58]=[CH:57][N:56]=[CH:55][CH:54]=2)[N:50]=[N:49][C:48]=1[O:59][CH3:60])=[O:35])([CH3:31])([CH3:30])[CH3:32]

Participants

Conditions

Temperature: -78 °C

Procedure

1.23 g methoxymethyltriphenylphoshonium chloride is suspended in 10 mL THF and cooled to −78° C. 2.20 mL butyllithium (1.6 M in hexanes) is added dropwise and the resulting mixture is stirred for 30 min at −78° C. and then warmed in an ice bath to 0° C. After addition of a solution of 734 mg 6-formyl-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester (see above) in 5 mL THF, the reaction mixture is heated to reflux for 5 hours. After cooling to rt, the reaction mixture is diluted with heptanes, washed with water, dried (MgSO4) and concentrated in vacuo. The resulting 280 mg crude enol ether is directly used in the next step.

Workup

temperaturewarmed in an ice bath to 0° C
temperaturethe reaction mixture is heated
temperatureto reflux for 5 hours
temperatureAfter cooling to rt
washwashed with water
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7bf3e54ab9a1423e8dedda95b8b729dc
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507734B2

Reaction notes

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