Methanol → HCID 67364123, compound

HRID 2046938Notes

Reaction equation

HRID 2046938 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH2:22][NH:23][CH2:24][CH2:25][CH:26]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11].[Si]([N:31]=[C:32]=[O:33])(C)(C)C.CO>C(Cl)Cl>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH2:22][N:23]([C:32]([NH2:31])=[O:33])[CH2:24][CH2:25][CH:26]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 70696Trimethylsilyl isocyanateHCID 67364015HCID 67364015, compound

Product 1

HCID 67364123HCID 67364123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-[(S)-1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5-(1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine (0.0030 g, 0.0077 mmol) in DCM (0.5 mL) was added a drop of TMS isocyanate. The reaction was stirred at 0° C. for 30 min. The solution was directly loaded onto Prep TLC (20×20 cm, silica gel, 5% MeOH in DCM) to afford the desired product. 1H-NMR (CD3OD, 400 MHz): δ=1.87 (d, J=7.1 Hz, 3 H), 2.22-2.44 (m, 2 H), 3.46-3.57 (m, 2H), 4.11-4.20 (m, 2 H), 5.27 (d, J=7.3 Hz, 1 H), 6.00 (t, J=2.0 Hz, 1 H), 7.11-7.24 (m, 1 H), 7.34 (dd, J=16.2, 1.8 Hz, 2 H), 8.19 (s, 1 H). MS (ES+): m/z 433.04/434.96 [MH+]. HPLC: tR=3.23 min (ZQ3, polar—5 min).

Sources & evidence

ORD record
ord-cf4fe81b5a1f43f890f9ac8a832a4746
Source dataset
uspto-grants-2013_11
Patent number
US08592448B2

Reaction notes

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