Methanol → HCID 10679834, compound

HRID 606831Notes

Reaction equation

CON(C)[C:4](=[O:19])[C:5]1[CH:10]=[C:9]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[N:7][CH:6]=1.[H-].C([Al+]CC(C)C)C(C)C.CO.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[C:13]1([C:12]#[C:11][C:9]2[CH:10]=[C:5]([CH:4]=[O:19])[CH:6]=[N:7][CH:8]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Charge an oven dried round bottom flask under nitrogen with a solution of N-methoxy-N-methyl-5-phenylethynylnicotinamide (2.00 g, 7.51 mmol), (prepared essentially as described in PREPARATION 2), in anhydrous toluene (20 mL) and cool to −78° C. Add a 1 M solution of diisobutylaluminum hydride in toluene (18 mL, 18 mmol) dropwise over 30 min and stir for an additional 30 min. Rapidly add methanol (15 mL) and warm to room temperature. Pour the reaction mixture into 100 mL of a saturated aqueous solution of Rochelle salt (potassium sodium tartrate) and stir vigorously for about 30 min. Upon standing, separate the organic layer, dry (magnesium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 50:50 hexanes:ethyl acetate, to obtain the title compound as a white solid (1.2 g, 77%).

Workup

additionCharge an oven
custom(prepared essentially
stirringstir vigorously for about 30 min
customseparate the organic layer
dry with materialdry (magnesium sulfate)
filtrationfilter
concentrationconcentrate
customPurify the residue by silica gel chromatography
washeluting with 50:50 hexanes

Sources & evidence

ORD record: ord-490c228247214337931ebda09b5b89a6
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915424B2

Reaction notes

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