4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 3-[(S)-1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5-pyridin-4-yl-1H-pyrrolo[2,3-b]pyridine

HRID 2046939Notes

Reaction equation

HRID 2046939 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.CC1(C)C(C)(C)OB([C:55]2[CH:60]=[CH:59][N:58]=[CH:57][CH:56]=2)O1>>[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:55]3[CH:60]=[CH:59][N:58]=[CH:57][CH:56]=3)[CH:33]=2)[NH:25][CH:26]=1)[CH3:36]

Participants

3

Reactant 2

HCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)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 ester

Product 1

HCID 673656683-[(S)-1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5-pyridin-4-yl-1H-pyrrolo[2,3-b]pyridine

Procedure

Example 68 was synthesized according to the Suzuki coupling method described above for the synthesis of example 66, using ((S)-1-{5-Bromo-3-[(S)-1-(2,6-dichloro-3-fluorophenyl)ethyl]pyrrolo[2,3-b]pyridine-1-carbonyl}-3-methyl-butyl)-carbamic acid 9H-fluoren-9-ylmethyl ester and 4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)pyridine, except that the crude product was purified by HPLC. 1H NMR (400 MHz, CD3OD): δ 8.48-8.59 (m, 3 H), 7.61 (d, J=2.0 Hz, 1H), 7.52 (dd, J=4.5, 1.5 Hz, 2H), 7.46-7.49 (m, 2 H), 7.20 (t, J=8.7 Hz, 1H), 5.34 (q, J=7.3 Hz, 1H), 1.91 (d, J=7.3 Hz, 3H). MS (ES+): m/z=386.19, 388.17 (100, 88) [MH+]. HPLC: tR=0.94 min (HPLC-ACQUITY, Purity).

Workup

  1. customExample 68 was synthesized
  2. customdescribed above for the synthesis of example 66
  3. customexcept that the crude product was purified by HPLC

Sources & evidence

ORD record
ord-9afa3d1e532544ef8370b11f7c5bc43f
Source dataset
uspto-grants-2013_11
Patent number
US08592448B2

Reaction notes

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