3-[1-(2,6-Dichlorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine → HCID 67364074, compound

HRID 2046944Notes

Reaction equation

HRID 2046944 reaction equation
C1C2C(COC(=O)N[C@H](C([N:25]3[C:29]4=[N:30][CH:31]=[C:32](Br)[CH:33]=[C:28]4[C:27]([C@@H:35]([C:37]4[C:42]([Cl:43])=[CH:41][CH:40]=[C:39]([F:44])[C:38]=4[Cl:45])[CH3:36])=[CH:26]3)=O)CC(C)C)C3C(=CC=CC=3)C=2C=CC=1.Cl.CC1(C)C(C)(C)OB([C:56]2[CH:57]=[N:58][N:59]([CH:61]3[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]3)[CH:60]=2)O1.ClC1C=CC=C(Cl)C=1C(C1C2C(=NC=C(C3C=NN(C4CCNCC4)C=3)C=2)NC=1)C>>[Cl:45][C:38]1[C:39]([F:44])=[CH:40][CH:41]=[C:42]([Cl:43])[C:37]=1[C@H:35]([C:27]1[C:28]2[C:29](=[N:30][CH:31]=[C:32]([C:56]3[CH:57]=[N:58][N:59]([CH:61]4[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]4)[CH:60]=3)[CH:33]=2)[NH:25][CH:26]=1)[CH3:36]

Participants

4

Reactant 3

HCID 462152983-[1-(2,6-Dichlorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineHCID 58431443((S)-1-{5-Bromo-3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]pyrrolo[2,3-b]pyridine-1-carbonyl}-3-methylbutyl)-carbamic acid 9H-fluoren-9-ylmethyl esterHCID 667591824-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine hydrochloride

Product 1

HCID 67364074HCID 67364074, compound

Procedure

((S)-1-{5-Bromo-3[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]-pyrrolo[2,3-b]pyridine-1-carbonyl}-3-methylbutyl)carbamic acid 9H-fluoren-9-ylmethyl ester was treated with 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrazol-1-yl]piperidine hydrochloride according to typical Suzuki coupling procedure described for synthesis of 3-[1-(2,6-Dichlorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine in example 1, to give the title compound. 1H NMR (400 MHz, DMSO-d6): δ=1.70-1.80 (m, 2H), 1.83 (d, J=7.1 Hz, 3H), 1.94 (dd, J=11.6, 2.0 Hz, 2H), 2.08 (br s, 1H), 2.57 (td, J=12.3, 2.3 Hz, 2H), 3.03 (ddd, J=12.6, 2.9, 2.7 Hz, 2H), 4.17 (tt, J=11.6, 4.1 Hz, 1H), 5.16 (q, J=7.2 Hz, 1H), 7.33 (d, J=1.8 Hz, 1H), 7.36-7.44 (m, 2H), 7.48-7.65 (m, 1H), 7.56 (d, J=0.5 Hz, 1H), 8.03 (s, 1H), 8.39 (d, J=2.0 Hz, 1H), 11.51 (d, J=1.8 Hz, 1H). MS (ES+): m/z 458.07/460.05 (100/70) [MH+]. HPLC: tR=2.53 min (ZQ3, polar—5 min).

Sources & evidence

ORD record
ord-0e99d5f428b649f280f6e0cf10585503
Source dataset
uspto-grants-2013_11
Patent number
US08592448B2

Reaction notes

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