Formaldehyde → HCID 66933773, compound

HRID 1425586Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:9][CH:8]=3.[CH2:23]=O.C[O-].[Na+].[BH4-].[Na+].[OH-].[Na+]>CO>[CH2:16]([O:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH3:23])=[CH:14][C:13]2=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 3-amino-6-(benzyloxy)-9H-carbazole 3 (90 mg, 0.31 mmol) and paraformaldehyde (47 mg, 1.57 mmol) in MeOH (20 mL) was added a solution of NaOMe in MeOH (0.32 mL, 1.56 mmol). The resulting mixture was heated at 80° C. for 1 h, then NaBH4 (59 mg, 1.55 mmol) was added. The resulting mixture was heated at 80° C. for 2 hrs, and then cooled to room temperature. To this solution was added NaOH (1 N, 30 mL). The mixture was then extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried (MgSO4), filtered. The filtrate was concentrated in vacuo to give a brown solid (93 mg, 100%). It was used directly in the next step without any further purification. 1H NMR (acetone-d6, 400 MHz) δ: 9.68 (br s, 1H), 7.67 (d, J=2.4 Hz, 1H), 7.53 (d, J=7.6 Hz, 2H), 7.20-7.42 (m, 6H), 7.03 (dd, J=8.8, 2.4 Hz, 1H), 6.79 (dd, J=8.4, 2.4 Hz, 1H), 5.17 (s, 2H), 2.85 (s, 3H). MS: m/z=303 (M+H+)+.

Workup

temperatureThe resulting mixture was heated at 80° C. for 2 hrs
temperaturecooled to room temperature
extractionThe mixture was then extracted with CH2Cl2 (3×20 mL)
dry with materialThe combined organic layers were dried (MgSO4)
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-ad53edb6a4b74fa594896e84161cb228
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08932557B2

Reaction notes

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