Methoxymethyl-triphenylphosphonium chloride → HCID 67111633, compound

HRID 1177546Notes

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.[F:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[C:38]1[S:39][C:40]2[C:45]([N:46]=1)=[CH:44][CH:43]=[C:42]([C:47]1([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[CH2:49][CH2:48]1)[N:41]=2)C=O>C1COCC1>[F:29][C:30]1[CH:31]=[C:32]([CH:24]=[CH:4][O:3][CH3:2])[CH:35]=[CH:36][C:37]=1[C:38]1[S:39][C:40]2[C:45]([N:46]=1)=[CH:44][CH:43]=[C:42]([C:47]1([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[CH2:48][CH2:49]1)[N:41]=2

Participants

Conditions

Temperature: 0 °C

Procedure

To (methoxymethyl)triphenylphosphonium chloride (1.0 g, 2.93 mmol) was added THF (26 mLl) before it was cooled to 0° C.; butyllithium (2.5 M in hexanes, 1.28 ml, 3.20 mmol) was then added and stirred for 15 min before 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde (1.00 g, 2.67 mmol) in THF (26 ml) was added to the reaction mixture. The reaction mixture was allowed to warm to ambient temperature and stir for 1 h to give 2-(2-fluoro-4-(2-methoxyvinyl)phenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine after flash chromatography. MS (ESI) m/z: Calculated: 402.1; Observed: 403.1 (M++H).

Workup

additionwas added to the reaction mixture
temperatureto warm to ambient temperature

Sources & evidence

ORD record: ord-1b68103eae874d779ab166cc450a60e8
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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