4-(Benzyloxy)-3-methylbenzaldehyde → HCID 178493877, compound

HRID 253286Notes

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[C:4]([CH3:11])[C:3]=1[C:12]1[C:13]([O:20][CH3:21])=[C:14]([OH:19])[CH:15]=[C:16]([F:18])[CH:17]=1.[CH2:22]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][C:31]=1[CH3:38])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(=O)C>[CH3:8][C:7]([N:6]1[C:2]2[N:1]=[C:34]([C:33]3[CH:36]=[CH:37][C:30]([O:29][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:31]([CH3:38])[CH:32]=3)[C:17]3[C:16]([F:18])=[CH:15][C:14]([OH:19])=[C:13]([O:20][CH3:21])[C:12]=3[C:3]=2[C:4]([CH3:11])=[N:5]1)([CH3:9])[CH3:10]

Participants

Conditions

Temperature: 120 °C

Procedure

To 3-[5-amino-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazol-4-yl]-5-fluoro-2-(methyloxy)phenol (150 mg, 0.51 mmol) was added 4-benzyloxy-3-methylbenzaldehyde (115 mg, 0.51 mmol) and acetic acid (2 mL). The mixture was heated to 120° C. and stirred overnight. The acetic acid was removed in vacuo. The residue was purified by flash chromatography (70% hexanes, 30% ethyl acetate) to provide 3-(1,1-dimethylethyl)-6-fluoro-1-methyl-9-(methyloxy)-5-{3-methyl-4-[(phenylmethyl)oxy]phenyl}-3H-pyrazolo[3,4-c]isoquinolin-8-ol (207 mg, 0.42 mmol, 81% yield) as an orange foam. 1H NMR (400 MHz, CDCl3): δ 7.52-7.35 (m, 7H), 6.99 (br d, 1H), 6.85 (d, 1H), 5.17 (s, 2H), 3.82 (s, 3H), 2.89 (s, 3H), 2.39 (s, 3H), 1.88 (s, 9H); MS (EI) for C30H30FN3O3: 500 (MH+).

Workup

customThe acetic acid was removed in vacuo
customThe residue was purified by flash chromatography (70% hexanes, 30% ethyl acetate)

Sources & evidence

ORD record: ord-04e48c79823c4d538a276f459c355dcc
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872014B2

Reaction notes

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