3-Iodo-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine → [5-(5-Chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(6-methoxy-pyridin-3-ylmethyl)-amine

HRID 1024267Notes

Reaction equation

HRID 1024267 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([Si](C(C)C)(C(C)C)C(C)C)[C:5]2=[N:6][CH:7]=1.C(OC(=O)[N:28]([C:38]1[CH:43]=[CH:42][C:41]([CH:44]=O)=[C:40]([F:46])[N:39]=1)[CH2:29][C:30]1[CH:31]=[N:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)(C)(C)C.IC1C2C(=NC=CC=2)N([Si](C(C)C)(C(C)C)C(C)C)C=1.C(OC(=O)N(CC1C(F)=CC=C(NS(CCC)(=O)=O)C=1F)C1C=CC(C=O)=CN=1)(C)(C)C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:44][C:41]3[CH:42]=[CH:43][C:38]([NH:28][CH2:29][C:30]4[CH:31]=[N:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=4)=[N:39][C:40]=3[F:46])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 242292273-Iodo-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridineHCID 57619209(6-Fluoro-5-formyl-pyridin-2-yl)-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester2×HCID 57619377[2,6-Difluoro-3-(propane-1-sulfonylamino)-benzyl]-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl esterHCID 580879285-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine2×

Product 1

HCID 24952876[5-(5-Chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(6-methoxy-pyridin-3-ylmethyl)-amine

Procedure

respectively, were prepared following the protocol of Scheme 178. P-0259 was prepared by replacing 3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine 96 with 5-chloro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine in Step 1 (MS [M+H+]+=506.1). P-0378 was prepared by replacing [2,6-difluoro-3-(propane-1-sulfonylamino)-benzyl]-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester 560 with (6-Fluoro-5-formyl-pyridin-2-yl)-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester 572 (prepared as described in Example 60, Scheme 177) in Step 1 (MS [M+H+]+=364.1). P-0379 was prepared by replacing both azaindole 96 with 5-chloro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine and aldehyde 560 with aldehyde 572 in Step 1 (MS [M+H+]+=400.0).

Workup

  1. customrespectively, were prepared
  2. customP-0259 was prepared
  3. customP-0378 was prepared
  4. customP-0379 was prepared

Sources & evidence

ORD record
ord-7b60da07617748799a5f568190ed7765
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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