Toluene → 5-(3-Fluorophenylethynyl)-pyridine-3-carbaldehyde

HRID 606870Notes

Reaction equation

HRID 606870 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[F:18][C:19]1[CH:20]=[C:21]([C:25]#[C:26][C:27]2[CH:28]=[N:29][CH:30]=[C:31]([CH:38]=2)[C:32](N(OC)C)=[O:33])[CH:22]=[CH:23][CH:24]=1>>[F:18][C:19]1[CH:20]=[C:21]([C:25]#[C:26][C:27]2[CH:38]=[C:31]([CH:32]=[O:33])[CH:30]=[N:29][CH:28]=2)[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 866224675-(3-Fluorophenylethynyl)-N-methoxy-N-methylnicotinamide

Product 1

HCID 860764545-(3-Fluorophenylethynyl)-pyridine-3-carbaldehydeYield 64%

Procedure

Prepare essentially as described in EXAMPLE 5 using a 1 M solution of diisobutylaluminum hydride in toluene (1.2 mL, 1.20 mmol), 5-(3-fluorophenylethynyl)-N-methoxy-N-methylnicotinamide, (prepared as described in PREPARATION 18), (170 mg, 0.60 mmol) to give the title compound (86 mg, 64%).

Workup

  1. customPrepare essentially

Sources & evidence

ORD record
ord-933f2c4ff71343acbf7a0789cfff2a80
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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